DE1542893A1 - Unkrautbekaempfungsmittel und Verfahren zur Unkrautbekaempfung - Google Patents
Unkrautbekaempfungsmittel und Verfahren zur UnkrautbekaempfungInfo
- Publication number
- DE1542893A1 DE1542893A1 DE19651542893 DE1542893A DE1542893A1 DE 1542893 A1 DE1542893 A1 DE 1542893A1 DE 19651542893 DE19651542893 DE 19651542893 DE 1542893 A DE1542893 A DE 1542893A DE 1542893 A1 DE1542893 A1 DE 1542893A1
- Authority
- DE
- Germany
- Prior art keywords
- dinitroindane
- hydrogen
- weed control
- dimethyl
- tetramethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 241000196324 Embryophyta Species 0.000 title claims description 50
- 238000000034 method Methods 0.000 title claims description 27
- -1 1, 1,4,5-tetramethyl-7-isopropylindane Chemical compound 0.000 claims description 27
- 239000004480 active ingredient Substances 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 239000004009 herbicide Substances 0.000 claims description 13
- 239000002689 soil Substances 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- AQCZJJPUSVSJSD-UHFFFAOYSA-N 2-ethyl-1,1,3,3,5-pentamethyl-4,6-dinitro-2H-indene Chemical compound CC1(C(C(C2=C(C(=C(C=C12)[N+](=O)[O-])C)[N+](=O)[O-])(C)C)CC)C AQCZJJPUSVSJSD-UHFFFAOYSA-N 0.000 claims description 6
- ZEBRPKFNGUEPCD-UHFFFAOYSA-N 3,3,5,7-tetramethyl-4,6-dinitro-1,2-dihydroindene Chemical compound CC1=C([N+]([O-])=O)C(C)=C2CCC(C)(C)C2=C1[N+]([O-])=O ZEBRPKFNGUEPCD-UHFFFAOYSA-N 0.000 claims description 6
- RWXBOLULRMRMJB-UHFFFAOYSA-N 5-ethyl-1,1,3,3-tetramethyl-4,6-dinitro-2H-indene Chemical compound CC1(CC(C2=C(C(=C(C=C12)[N+](=O)[O-])CC)[N+](=O)[O-])(C)C)C RWXBOLULRMRMJB-UHFFFAOYSA-N 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- YCDQPESZQWYLTK-UHFFFAOYSA-N 3,3-dimethyl-4,6-dinitro-5-propan-2-yl-1,2-dihydroindene Chemical compound CC1(CCC2=CC(=C(C(=C12)[N+](=O)[O-])C(C)C)[N+](=O)[O-])C YCDQPESZQWYLTK-UHFFFAOYSA-N 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 150000002431 hydrogen Chemical group 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- YZHUMGUJCQRKBT-UHFFFAOYSA-M sodium chlorate Chemical compound [Na+].[O-]Cl(=O)=O YZHUMGUJCQRKBT-UHFFFAOYSA-M 0.000 claims 4
- 239000012876 carrier material Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 150000002468 indanes Chemical class 0.000 description 11
- 235000013603 Digitaria ischaemum Nutrition 0.000 description 9
- 241000035632 Digitaria ischaemum Species 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 238000006722 reduction reaction Methods 0.000 description 8
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 241000209202 Bromus secalinus Species 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 229910017604 nitric acid Inorganic materials 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N benzocyclopentane Natural products C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 5
- 230000002363 herbicidal effect Effects 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000009331 sowing Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- 241001355178 Setaria faberi Species 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 238000006396 nitration reaction Methods 0.000 description 4
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical group CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 3
- 244000088461 Panicum crus-galli Species 0.000 description 3
- 235000011999 Panicum crusgalli Nutrition 0.000 description 3
- 240000002439 Sorghum halepense Species 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 230000009965 odorless effect Effects 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 150000003440 styrenes Chemical class 0.000 description 3
- PJPNYZCIGFQVQG-UHFFFAOYSA-N 3,3,5,7-tetramethyl-1,2-dihydroindene Chemical compound CC1=CC(C)=CC2=C1CCC2(C)C PJPNYZCIGFQVQG-UHFFFAOYSA-N 0.000 description 2
- MKSQYPPZMHJESS-UHFFFAOYSA-N 5-ethyl-3,3-dimethyl-4,6-dinitro-1,2-dihydroindene Chemical compound CC1(CCC2=CC(=C(C(=C12)[N+](=O)[O-])CC)[N+](=O)[O-])C MKSQYPPZMHJESS-UHFFFAOYSA-N 0.000 description 2
- 244000237956 Amaranthus retroflexus Species 0.000 description 2
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 2
- 241000209764 Avena fatua Species 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- 241001478727 Salvinia auriculata Species 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006352 cycloaddition reaction Methods 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- IWIWGFMIKABCFO-UHFFFAOYSA-N 1,1,3,3-tetramethyl-2h-indene Chemical compound C1=CC=C2C(C)(C)CC(C)(C)C2=C1 IWIWGFMIKABCFO-UHFFFAOYSA-N 0.000 description 1
- CPLBLNGVYBSVPU-UHFFFAOYSA-N 1,3,3-trimethyl-1,2-dihydroindene Chemical compound C1=CC=C2C(C)CC(C)(C)C2=C1 CPLBLNGVYBSVPU-UHFFFAOYSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- RHBKJVRQCIRZGE-UHFFFAOYSA-N 2,3,3-trimethyl-1,2-dihydroindene Chemical compound C1=CC=C2C(C)(C)C(C)CC2=C1 RHBKJVRQCIRZGE-UHFFFAOYSA-N 0.000 description 1
- RJRNJUIFZKGOCP-UHFFFAOYSA-N 2-ethyl-1,1,3,3,5-pentamethyl-2h-indene Chemical compound C1=C(C)C=C2C(C)(C)C(CC)C(C)(C)C2=C1 RJRNJUIFZKGOCP-UHFFFAOYSA-N 0.000 description 1
- UTTMVTDJCFSOFF-UHFFFAOYSA-N 3,3-dimethyl-1,2-dihydroindene Chemical compound C1=CC=C2C(C)(C)CCC2=C1 UTTMVTDJCFSOFF-UHFFFAOYSA-N 0.000 description 1
- HNGSTGNHMZWIPG-UHFFFAOYSA-N 3,3-dinitro-1,2-dihydroindene Chemical class C1=CC=C2C([N+](=O)[O-])([N+]([O-])=O)CCC2=C1 HNGSTGNHMZWIPG-UHFFFAOYSA-N 0.000 description 1
- FSBIQEDMEKAAMA-UHFFFAOYSA-N 3,4,7-trimethyl-2,3-dihydroinden-1-one Chemical compound CC1=CC=C(C)C2=C1C(C)CC2=O FSBIQEDMEKAAMA-UHFFFAOYSA-N 0.000 description 1
- GCZQTQUHBZZQAC-UHFFFAOYSA-N 4,7-dimethyl-2,3-dihydroinden-1-one Chemical compound CC1=CC=C(C)C2=C1CCC2=O GCZQTQUHBZZQAC-UHFFFAOYSA-N 0.000 description 1
- KZQAWSCKFDNZOT-UHFFFAOYSA-N 5-ethyl-1,1,3,3-tetramethyl-2H-indene Chemical compound C(C)C=1C=C2C(CC(C2=CC1)(C)C)(C)C KZQAWSCKFDNZOT-UHFFFAOYSA-N 0.000 description 1
- 235000007320 Avena fatua Nutrition 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical class C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- 240000006122 Chenopodium album Species 0.000 description 1
- 235000009344 Chenopodium album Nutrition 0.000 description 1
- 241001448825 Elodea canadensis Species 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 238000005644 Wolff-Kishner reduction reaction Methods 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000000889 atomisation Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000006210 cyclodehydration reaction Methods 0.000 description 1
- HHNHBFLGXIUXCM-GFCCVEGCSA-N cyclohexylbenzene Chemical compound [CH]1CCCC[C@@H]1C1=CC=CC=C1 HHNHBFLGXIUXCM-GFCCVEGCSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 150000002469 indenes Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 238000005121 nitriding Methods 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/06—Compounds containing nitro groups bound to a carbon skeleton having nitro groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/562—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with nitrogen as the only hetero atom
- C07C45/565—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with nitrogen as the only hetero atom by reaction with hexamethylene-tetramine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/542—Alkylated benzaldehydes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/546—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/782—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic
- C07C49/792—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic containing rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US399904A US3393994A (en) | 1964-09-28 | 1964-09-28 | Method of controlling weeds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1542893A1 true DE1542893A1 (de) | 1970-07-23 |
Family
ID=23581425
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19651542893 Pending DE1542893A1 (de) | 1964-09-28 | 1965-09-17 | Unkrautbekaempfungsmittel und Verfahren zur Unkrautbekaempfung |
| DE1542892A Granted DE1542892B2 (de) | 1964-09-28 | 1965-09-17 | Unkrautbekämpfungsmittel auf Basis von Indanylketonen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1542892A Granted DE1542892B2 (de) | 1964-09-28 | 1965-09-17 | Unkrautbekämpfungsmittel auf Basis von Indanylketonen |
Country Status (13)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3499751A (en) * | 1966-07-05 | 1970-03-10 | Givaudan Corp | Method and composition for controlling weeds with acylated tetrahydronaphthalene |
| US4284819A (en) * | 1978-10-20 | 1981-08-18 | International Flavors & Fragrances Inc. | Acetyl hydrindacenes, acetyl indanes, mixtures of same, processes for preparing same and organoleptic uses thereof |
| US4332970A (en) * | 1980-06-05 | 1982-06-01 | International Flavors & Fragrances Inc. | Acetyl hydrindacenes, acetyl indanes, mixtures of same, processes for preparing same and organoleptic uses thereof |
| US5185318A (en) * | 1989-06-30 | 1993-02-09 | Firmenich S.A. | Aromatic compounds, a process for preparation thereof and use of same as perfuming ingredients |
| EP0405427B1 (fr) * | 1989-06-30 | 1995-03-29 | Firmenich Sa | Nouveaux composés aromatiques, leur procédé de préparation et leur utilisation à titre d'ingrédients parfumants |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB796129A (en) * | 1953-10-09 | 1958-06-04 | Polak Frutal Works | Polyalkylindane derivatives and process for manufacturing the same |
| US3152192A (en) * | 1961-05-02 | 1964-10-06 | Givandan Corp | Process for preparing trialkyl-1, 1-dimethylindans |
| US3240929A (en) * | 1962-09-14 | 1966-03-15 | Gen Signal Corp | Control system for railway trains |
-
1964
- 1964-09-28 US US399904A patent/US3393994A/en not_active Expired - Lifetime
-
1965
- 1965-09-12 IL IL24303A patent/IL24303A/xx unknown
- 1965-09-15 CH CH1287365A patent/CH472184A/de not_active IP Right Cessation
- 1965-09-17 DE DE19651542893 patent/DE1542893A1/de active Pending
- 1965-09-17 DE DE1542892A patent/DE1542892B2/de active Granted
- 1965-09-22 AT AT863865A patent/AT258645B/de active
- 1965-09-27 BR BR173495/65A patent/BR6573495D0/pt unknown
- 1965-09-27 ES ES0317860A patent/ES317860A1/es not_active Expired
- 1965-09-27 GB GB41021/65A patent/GB1122066A/en not_active Expired
- 1965-09-27 BE BE670184D patent/BE670184A/xx unknown
- 1965-09-28 DK DK498565AA patent/DK117871C/da active
- 1965-09-28 FI FI2305/65A patent/FI40840B/fi active
- 1965-09-28 NL NL656512565A patent/NL143111B/xx unknown
-
1969
- 1969-12-31 MY MY1969195A patent/MY6900195A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US3393994A (en) | 1968-07-23 |
| NL143111B (nl) | 1974-09-16 |
| IL24303A (en) | 1969-02-27 |
| DK117871C (da) | 1970-11-09 |
| NL6512565A (enrdf_load_stackoverflow) | 1966-03-29 |
| GB1122066A (en) | 1968-07-31 |
| AT258645B (de) | 1967-12-11 |
| BE670184A (enrdf_load_stackoverflow) | 1966-03-28 |
| BR6573495D0 (pt) | 1973-02-27 |
| DE1542892C3 (enrdf_load_stackoverflow) | 1975-03-13 |
| DE1542892A1 (de) | 1970-07-23 |
| FI40840B (enrdf_load_stackoverflow) | 1969-02-28 |
| ES317860A1 (es) | 1966-05-16 |
| DE1542892B2 (de) | 1974-07-18 |
| CH472184A (de) | 1969-05-15 |
| MY6900195A (en) | 1969-12-31 |
| DK117871B (enrdf_load_stackoverflow) | 1970-06-08 |
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